I'm sorry but this is not a good question as there is no answer to it. It's like dividing by zero. If you have access to food and housing and $500 on top of that and you want to spend $500 on shoes then I think you can afford them. Net worth is pretty meaningless unless you are talking about retiring or becoming disabled.

Actually, there are many answers to it. In your case, you answered $500. ie: You're ok with spending your last dime on shoes provided you have food and housing covered. Based on other replies, you might find it interesting that someone else might not dare spend $500 on shoes until he's got $25k in the bank. Yet another person might not even consider spending $500 on shoes before he's got $1,500,000 saved. And so forth...

Based on other replies, you might find it interesting that someone else might not dare spend $500 on shoes until he's got $25k in the bank. Yet another person might not even consider spending $500 on shoes before he's got $1,500,000 saved. And so forth...

Exactly. As many different answers as there are people, therefore not quantifiable. Not to be too harsh, but I don't find it that interesting, because it's something I think is obvious. I agree that many people think that $500 is some sort of wild indulgence. However, if you have to wear dress shoes to work anyway, $500 on shoes probably is a better use of funds than saying buying a $500 ipad. FA

Is this a question of buying a single pair of $500+ shoes that you will consider the crown jewel in your wardrobe? Or is this a question of creating a rotation of $500+ shoes?

Honestly if you have a passion for it almost anyone can save up enough to buy a single pair of $500 shoes. However, you will more likely than need a steady and sizable salary to buy a new pair of $500+ shoes every couple of months and consider that your norm.

As a new college grad (and drawing an according salary) I generally hesitate to spend that much on shoes. However, if I saw some that struck my fancy to that extent I would suck it up, take out my wallet and walk around with a shit eating grin each time I put them on my feet.

Also, might I ask who you know that will A. know that you spent $500+ on a pair of shoes and B. judge you for not having enough money to make the purchase at the same time?

Another vote for "this is a meaningless question." If income > expenses + savings goals + other discretionary spending + $500 for shoes, then you have enough money for them. Your net worth is like the integral factor of that equation over time, sort of useless for deciding if you can "afford" them or not. Perhaps your savings goals would be higher when you had a lower net worth, but still a dumb question.

I think it's a good benchmark for that "next next level"
Where someone might react "Holy fuck, are you kidding? For SHOES? Are they gold plated?"

1) $75-$100 (A typical man's nice shoes)
2) $250 (AE, etc. Most men never arrive at this)
3) $500 (Getting "very serious" about shoes. He reads about this shit. I doubt even 1% of men ever spend this much)
4) $1000 (At this point, shoes are part of your core identity and reason for being)

Another vote for "this is a meaningless question." If income > expenses + savings goals + other discretionary spending + $500 for shoes, then you have enough money for them. Your net worth is like the integral factor of that equation over time, sort of useless for deciding if you can "afford" them or not. Perhaps your savings goals would be higher when you had a lower net worth, but still a dumb question.

For example, if a guy had, say, $1000 in the bank,
would you think it's reasonable for him to buy $500 shoes?

Some people would say that's absolutely mad.
Others would see absolutely nothing wrong with that.

So, the question again, at what number would you think a guy is mad for spending $500 on shoes.
Again, $501 is a perfectly valid answer, and it reflects volumes. Just understand, that is not the only answer people will give.